5. June 17, 1994

Heroes fall, but none in the American sporting world has fallen further than O.J. Simpson. And his fall hit especially hard for the Buffalo Bills, a franchise steeped in history but largely devoid of a megastar. Except O.J. Before June 17, 1994, O.J. Simpson was the star of stars – Baryshnikov on the field, Bogart off it. And while he rose to fame in Los Angeles and finished his career in his hometown of San Francisco, Buffalo could claim him as its own. But then the Bronco chase happened and everything after (and before) that, and America’s brightest crossover star suddenly became persona non grata, which meant Buffalo could no longer point to its greatest hero with any sort of pride. O.J. still remains a member of the Bills’ Wall of Fame, but if anything it might as well be a reminder that Santa Claus isn’t real.

4. Thurman Thomas loses his helmet before Super Bowl XXVI

When you lose four straight Super Bowls, you’re going to be in position to have some not-so-enjoyable moments, and Thurman Thomas, despite being an all-time great Buffalo Bill, just happens to be the center of two of these. Thomas led the AFC in rushing during the ‘91 regular season and was expected to be a big part of the game, but before the start of Super Bowl XXVI against the Washington Redskins, he lost his helmet. While searching, Thomas missed most of the Bills’ first offensive series, and they went three-and-out to open the game. Did this have an impact on the outcome of the game? Well, Thomas finished with just 13 yards on 10 carries, and surely that had an impact in the Bills losing 37-24.

3. Thurman Thomas fumbles the ball

Having lost three Super Bowls in a row, Buffalo and the Bills were feeling optimistic coming out of halftime of Super Bowl XXVIII with a 13-6 lead over the Dallas Cowboys. But that optimism ended less than a minute into the third quarter when Leon Lett, the goat of Super Bowl XXVII, stripped Thurman Thomas of the ball, which James Washington picked up and returned 46 yards for a touchdown. From there, the Cowboys scored 24 unanswered points to win their second straight championship and, in the process, hand the Bills their fourth straight Super Bowl defeat.

2. The Music City Miracle

Never has a special teams play had more significance than in the 2000 AFC wildcard game between the Bills and Tennessee Titans. Leading 16-15 with 14 seconds to play, all the Bills needed to do was hold the Titans back on a routine kickoff. Kevin Dyson had other plans, however, as he took a lateral pass from tight end Frank Wycheck – was it a lateral? – 75 yards to the end zone as time expired. Titans 22, Bills 16. Officials – namely Phil Luckett, he of the infamous Steelers-Lions coin toss flub – reviewed the play for nearly two minutes to determine if Wycheck’s lateral was indeed a lateral and not an illegal forward pass. Upon further review, they ruled the play legal. Touchdown Titans. Ballgame. And to date, the Bills have not made the postseason since.

1. Wide Right

In perhaps one of the most heartbreaking sports moments of all time, the Bills squandered their first and best shot at Super Bowl glory when they missed a late field goal attempt. Trailing the New York Giants by one point with eight seconds left in Super Bowl XXV, Bills kicker Scott Norwood’s 47-yard attempt sailed wide right. It had plenty of distance, just not the accuracy. It was the Bills first of four consecutive Super Bowl loses, and turned out to be the closest they would get to winning one, as they lost by 13, 35 and 17 points in the Super Bowls to follow.